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Showing NP-Card for 2-Hydroxypyridine (NP0054953)

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Record Information
Version2.0
Created at2022-04-28 01:08:54 UTC
Updated at2022-04-28 01:08:54 UTC
NP-MRD IDNP0054953
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Hydroxypyridine
Description2-Hydroxypyridine, also known as 2-pyridone or alpha -pyridone, belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone. 2-Hydroxypyridine is a moderately basic compound (based on its pKa). It is well known to form hydrogen bonded structures somewhat related to the base-pairing mechanism found in RNA and DNA. Protic solvents also mediate the proton transfer during the tautomerisation. For example, to calculation of the energy difference of the two tautomers in a non-polar solution will lead to a wrong result if a large quantity of the substance is on the side of the dimer in an equilibrium. It is also a classic case of a molecule that exists as tautomers. Some publications only focus one of the two possible patterns, and neglect the influence of the other. The direct tautomerisation is not energetically favoured, but a dimerisation followed by a double proton transfer and dissociation of the dimer is a self catalytic path from one tautomer to the other. 2-Hydroxypyridine is found in Arabidopsis thaliana, Lotus corniculatus, Lotus creticus, Medicago sativa, Pogostemon cablin and Salvia divinorum. This colourless crystalline solid is used in peptide synthesis.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054953 (2-Hydroxypyridine)

 
  Mrv1652304202019402D          
 
  7  7  0  0  0  0            999 V2000
   11.1938   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -9.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9018   -9.5299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -7.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for NP0054953 (2-Hydroxypyridine)

     RDKit          3D

 12 12  0  0  0  0  0  0  0  0999 V2000
    2.3481   -1.0596   -0.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325   -0.5887   -0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7870    0.7682    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    1.2862    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569    0.4194   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -0.9211   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -1.4009   -0.2448 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190   -1.4689    0.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6682    1.4164    0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    2.3674    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819    0.8033    0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1036   -1.6217   -0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
M  END
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3D SDF for NP0054953 (2-Hydroxypyridine)

 
  Mrv1652304202019402D          
 
  7  7  0  0  0  0            999 V2000
   11.1938   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1938   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -9.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9018   -9.5299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743   -7.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -9.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7661   -8.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)

> <INCHI_KEY>
UBQKCCHYAOITMY-UHFFFAOYSA-N

> <FORMULA>
C5H5NO

> <MOLECULAR_WEIGHT>
95.0993

> <EXACT_MASS>
95.037113787

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.200287283659224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyridin-2-ol

> <ALOGPS_LOGP>
0.64

> <JCHEM_LOGP>
1.0464655973333332

> <ALOGPS_LOGS>
0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.700690095151401

> <JCHEM_PKA_STRONGEST_BASIC>
2.429271976905061

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
26.195499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-pyridone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0054953 (2-Hydroxypyridine)

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PDB for NP0054953 (2-Hydroxypyridine)
HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      20.895 -17.023   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.895 -15.483   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      19.552 -17.810   0.000  0.00  0.00           N+0
HETATM    4  O   UNK     0      22.217 -17.789   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.552 -14.716   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.230 -17.023   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.230 -15.483   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    7                                                       
CONECT    7    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0054953 (2-Hydroxypyridine)
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SMILES for NP0054953 (2-Hydroxypyridine)
OC1=CC=CC=N1
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INCHI for NP0054953 (2-Hydroxypyridine)
InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
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Synonyms
ValueSource
2-PyridinolChEBI
2-PyridoneChEBI
1-Hydroxy-2-pyridineHMDB
1H-Pyridin-2-oneHMDB
2(1H)-PyridinoneHMDB
2(1H)-PyridoneHMDB
2-OxopyridineHMDB
2-Pyridinol (acd/name 4.0)HMDB
2-PyridinoneHMDB
2-PyridolHMDB
alpha -PyridoneHMDB
alpha-PyridoneHMDB
Pyridin-2-olHMDB
Pyridone-2HMDB
2-Hydroxypyridine sodium saltHMDB
2-HydroxypyridineChEBI
Chemical FormulaC5H5NO
Average Mass95.0993 Da
Monoisotopic Mass95.03711 Da
IUPAC Namepyridin-2-ol
Traditional Name2-pyridone
CAS Registry NumberNot Available
SMILES
OC1=CC=CC=N1
InChI Identifier
InChI=1S/C5H5NO/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7)
InChI KeyUBQKCCHYAOITMY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
Lotus corniculatusLOTUS Database
Lotus creticusLOTUS Database
Medicago sativaLOTUS Database
Pogostemon cablinLOTUS Database
Salvia divinorumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyridines and derivatives  
Sub ClassHydropyridines  
Direct ParentPyridinones  
Alternative Parents
Substituents
  • Pyridinone
    • 

  • Dihydropyridine
    • 

  • Heteroaromatic compound
    • 

  • Lactam
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.64ALOGPS
logP1.05ChemAxon
logS0.53ALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)2.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.2 m³·mol⁻¹ChemAxon
Polarizability9.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013751  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007405  
Chemspider ID8537  
KEGG Compound IDC02502  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Pyridone  
METLIN IDNot Available
PubChem Compound8871  
PDB IDNot Available
ChEBI ID16540  
Good Scents IDNot Available
References
General References